Surfactants From Sulfonation Of Aromatic Ethers

Abstract

The present disclosure relates to surfactants formed from sulfonation of aromatic ethers. The example surfactant composition may include a sulfonated aromatic ether. The sulfonated aromatic ether may include an aromatic ring with substituents comprising an ether group and a sulfonic acid group or a salt of the sulfonic acid group. The ether group may be represented by the following formula: wherein R 1 is a linear or branched alkyl group having from 1 carbon atom to 20 carbon atoms; wherein each R 2 is individually a hydrogen or an alkyl group having from 1 carbon atom to 4 carbon atoms; and wherein n is a value from 0 to 8.

1 . A surfactant composition comprising:
 a sulfonated aromatic ether comprising an aromatic ring with substituents comprising an ether group and a sulfonic acid group or a salt of the sulfonic acid group, wherein the ether group is represented by the following formula:   
       
         
           
           
               
               
           
         
         wherein R 1  is a linear or branched alkyl group having from 1 carbon atom to 20 carbon atoms; 
         wherein each R 2  is individually a hydrogen or an alkyl group having from 1 carbon atom to 4 carbon atoms; and 
         wherein n is a value from 0 to 8. 
       
     
     
         2 . The surfactant composition of  claim 1 , wherein the aromatic ring is a six-membered monocyclic ring. 
     
     
         3 . The surfactant composition of  claim 1 , wherein the aromatic ring is a six-membered monocyclic ring with the ether group at the 1-position, the ether group at the 2-position, or the either group at the 1-position with an additional ether group at the 2-position. 
     
     
         4 . The surfactant composition of  claim 1 , wherein the aromatic ring is a six-membered monocyclic ring with the ether group at the 1-position and with the sulfonic acid group or the salt of the sulfonic acid group at any unsubstituted position on the six-member monocyclic ring. 
     
     
         5 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 3  is individually a hydrogen, the sulfonic acid group, the salt of the sulfonic acid group, an ether group of Formula (I), an alkyl group, an alkenyl group, a heteroatom-substituted alkyl group, a hetero-atom substituted alkenyl group, or a heteroatom; and 
         wherein at least one R 3  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         6 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen, the sulfonic acid group, or the salt of the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         7 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by at least one of the following formulae further having the sulfonic acid group or the salt of the sulfonic acid group at any one of the 3-position, the 4-position, 5-position and/or 6-position: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen, the sulfonic acid group, or the salt of the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         8 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen, the sulfonic acid group, or the salt of the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         9 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by at least one of the following formulae further having the sulfonic acid group or the salt of the sulfonic acid group at the 2-position, 4-position, 5-position and/or 6-position: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen, the sulfonic acid group, or the salt of the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         10 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen, the sulfonic acid group, or the salt of the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         11 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen or the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group. 
       
     
     
         12 . The surfactant composition of  claim 1 , wherein the aromatic ring is a 10-membered or 12-membered bicyclic ring. 
     
     
         13 . The surfactant composition of  claim 1 , wherein the sulfonated aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 4  is individually a hydrogen, the sulfonic acid group, or the salt of the sulfonic acid group; and 
         wherein at least one R 4  is the sulfonic acid group or the salt of the sulfonic acid group. 
       
     
     
         14 . A method of forming a surfactant composition comprising:
 reacting an aromatic ether with a sulfonating reagent to form the surfactant composition, wherein the aromatic ether comprises an ether group represented by the following formula:   
       
         
           
           
               
               
           
         
         wherein R 1  is a linear or branched alkyl group having from 1 carbon atom to 20 carbon atoms; 
         wherein each R 2  is individually a hydrogen or an alkyl group having from 1 carbon atom to 4 carbon atoms; and 
         wherein n is a value from 0 to 8, and
 wherein the surfactant composition comprises a sulfonated aromatic ether comprising an aromatic ring with substituents comprising the ether group and a sulfonic acid group. 
 
       
     
     
         15 . The method of  claim 14 , wherein the reacting occurs at a reaction temperature from about 60° C. to about 150° C. 
     
     
         16 . The method of  claim 14 , wherein the reacting occurs in the presence of a dichloro alkane. 
     
     
         17 . The method of  claim 14 , wherein the sulfonating reagent comprises a silica-sulfuric acid. 
     
     
         18 . The method of  claim 14  wherein the aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein each R 5  is a hydrogen, an ether group of Formula (I), an alkyl group, an alkenyl group, a heteroatom-substituted alkyl group, a hetero-atom substituted alkenyl group, or a heteroatom. 
       
     
     
         19 . The method of  claim 14 , wherein the aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         20 . The method of  claim 14 , wherein the aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         21 . The method of  claim 14 , wherein the aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         22 . The method of  claim 14 , wherein the aromatic ether is represented by the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         23 . The method of  claim 14 , wherein the aromatic ether comprises a 10-member or 12-member bicyclic ring. 
     
     
         24 . The method of  claim 14 , further comprising neutralizing the sulfonic acid group to form a salt of the sulfonic acid group.